Senior Engineering Manager

Summary

Join Headway's Trust Foundations team as a Senior Engineering Manager to lead a new Secure Defaults pod and protect sensitive user data. You will own the team's vision and long-term strategy for data security at scale, spearheading initiatives in data lineage, sensitive information classification, and next-generation RBAC. A key aspect is defining the roadmap for secure and compliant AI use. This is a critical leadership role to build a new team and immediately impact Headway's secure scaling. The ideal candidate is a security-minded leader passionate about developing engineers and fostering a culture of technical excellence. You will lead, develop, and mentor a team, own the team's strategy and roadmap, and develop future leaders. Headway offers a competitive compensation and benefits package.

Requirements

BS, MS in Computer Science or related field

Responsibilities

• Lead, develop, and mentor a team of 5+ engineers, guiding their career growth through continuous feedback and dedicated 1-1s, and support hiring as we scale engineering from 120 to 175+ in the coming year
• Own your team's strategy and roadmap, ensuring its alignment with broader company objectives and driving execution to deliver results
• Develop future leaders by identifying and mentoring aspiring technical leaders, contributing to the growth of talent across the entire engineering organization

Preferred Qualifications

• You have a track record of building and leading high-performing teams, with 5+ years of experience as an Engineering Manager built upon a 4-5+ year background as a hands-on Software Engineer
• You are a deep domain expert in data security architecture. You have proven, practical experience designing and delivering systems for data lineage, classification of sensitive data (like PHI), and de-identification at scale
• You think in platforms and primitives. You have a demonstrated history of building secure-by-default foundations (e.g., RBAC systems, data access layers) and internal tooling that empowers other engineering teams to move faster and more safely
• You are a forward-looking, strategic thinker. You have an informed perspective on the future of data security, including the challenges and opportunities of applying AI to solve these complex problems in a safe and compliant way
• You are a pragmatic partner with a strong product mindset. You know how to balance robust security principles with the needs of a rapidly scaling business and can collaborate effectively with stakeholders in Legal, Security, and Product to deliver clear business outcomes through your technical investments
• It's a nice to have if you've had prior experience with Python and React and working with AWS infrastructure
• It's a nice to have if you've had experience in health tech, building user-facing products

Benefits

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development